Naples Vacation Rentals
Apartments, homes, condos, and townhomes to elevate your stay in Florida’s Paradise Coast.
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Visit Naples
Ecotourists, art lovers, foodies, and water adventurers flock to Naples–the gem of Florida’s Paradise Coast. Sun-drenched weather, culture, and upscale offerings make this South Florida jewel the ideal getaway. Navigate the mangrove tunnels and paddle alongside resident manatee or venture out to kayak on the open water. Pack the sunscreen, a bestseller, and a chair to stake out the perfect dolphin-watching spot along the miles of sand. Anglers, Naples offers every kind of fishing where you can cast a line from a pier in the morning then head out and deep-sea fish or try your luck at one of the area’s lakes. Golfers can perfect their game at one of the area’s 90 courses–a true golfer’s paradise. Add in shopping, top-notch dining, and entertainment, Naples ticks all of the beach vacation boxes.
Your Naples Vacation, Your Way.
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Featured Naples
Vacation Rentals
Naples Beach
More than 10 miles of Gulf coastline entices beachcombers to find their favorite spot in the sand. Swimmers love to jump the waves, splash around, or get in some fitness in these calmer waters. Naples Pier is still a popular spot, despite suffering some recent damage. This spot is close to Downtown Naples and serves up points of access for kayakers and paddleboarders.
Vanderbilt Beach
Vanderbilt Beach’s popularity during peak season makes it a key spot for sun lovers and swimmers alike, so try to arrive before 10 am to snag a parking spot. Once you feel the soft, white sand under your feet and gaze at the turquoise waters, you’ll see why this North Naples spot earns its reputation as one of the town’s most stunning beaches.
Barefoot Beach
The perfect stretch of Naples coastline for people who want to escape the crowds and bathe in Florida sand and sun. Explore the more than two miles of azure coastline that sea turtles call home. Scour the shoreline to add to your shell collection or grab your kayak to explore the estuaries that weave through the park. Pack a picnic–no concession stands in this natural wonderland.
Island of Keewaydin
Nearby Marco Island
Fifth Avenue South
Upscale shopping and dining meet Florida outdoor living. This walkable retail haven acts as Naples’ unofficial Main Street and when you amble through the boutiques and shops that serve up an Old Florida vibe, you’ll see why Fifth Avenue South draws in locals and visitors alike. Relax with a cocktail or coffee at the area’s bars and cafes, or indulge in some of the area’s best cuisine. Want to check Fifth Avenue South out before you’re in town? The area even has its own podcast for you to learn about this Naples hub.
Third Street South
The 19th century Naples Pier, Gulf winds dancing across your face, a leisurely cocktail sipped al fresco? Third Street South’s offerings have delighted visitors and locals since the 19030s. The Florida sun gives life to lush landscaping that elevates the area and seasonal events like the summer Farmer’s Market and Semi-Annual Sidewalk sales might just make your stay more memorable.
Lowdermilk Park
Sand volleyball, a playground, picnic tables, gazebos for rent, and ADA beach access mats invite everyone to visit Lowdermilk Park for the perfect beach day. Open from 5 am to 11 pm.
Private Chef, Chef Anthony Santos
Indulge in a culinary journey with Chef Anthony Santos, who brings exquisite flavors and personalized service right to your table. With years of experience and a passion for crafting memorable dining experiences, Chef Anthony transforms any meal into an extraordinary event, perfect for intimate gatherings or special celebrations.
Learn more here.
Anchor Private Yacht Rentals
Set sail in luxury with a private yacht rental, offering options both with and without a captain to suit your preferences. Whether you prefer a guided tour or the freedom to explore at your own pace, these yachts promise an unforgettable experience on the open water.
Learn more here.
Bark of the Ark
Pure Florida’s popular Bark on the Ark, a dog friendly cruise is a monthly event for the whole family. The fun cruise takes guests and their pups aboard the M/V Edison Explorer for a sightseeing eco cruise along Naples Bay to Keewaydin Island. Cruises depart from Tin City, located at 1200 Fifth Ave. S., Naples.
Rising Tide Explorers
Rising Tide Explorers gives you the opportunity to experience some of Naples & Marco Island’s most beautiful natural areas with kayak rentals and exciting adventures led by the region’s only team of 100% active local biologist guides.
Naples Zoo
Whether you’re exploring with family, friends, or on a solo adventure, the Naples Zoo promises an enriching and heartwarming experience. Come join us for a day of discovery, where every step brings you closer to the fascinating world of wildlife.
Naples Pier
For the perfect blend of relaxation and excitement, the Naples Pier is the place to be. Whether you’re capturing a stunning sunset, savoring the coastal breeze, or simply immersing yourself in the vibrant atmosphere.
Naples Princess
Naples Princess Cruises offer opportunities to soak in the sunshine or enjoy the climate controlled air-conditioned salons as you cruise past the multi-million-dollar homes of Port Royal and see the sunset drop from the Gulf of Mexico in Naples Florida.
Extreme Boat Rentals in Naples
Discover hidden coves, race across the waves, and explore the Gulf of Mexico like never before.
Everglades from Naples
Embark on a wild expedition from Naples to the untamed beauty of the Everglades! Immerse yourself in the heart of Florida’s unique ecosystem, just a short drive from the charming streets of Naples.
Miss Naples Catamaran Cruise
Set sail for an unforgettable experience with Miss Naples Catamaran Cruise! Departing from the picturesque shores of Naples, this catamaran journey promises a perfect blend of luxury, relaxation, and the mesmerizing beauty of the Gulf of Mexico.
Cruisin Tiki’s
Naples Depot and Train Museum
The mission of the Collier County Museum Division is to engage residents and visitors in appreciation and understanding of our communities’ unique heritage and cultural development.
Koresha State Park
Koresha State Park is a picturesque natural reserve known for its diverse wildlife, scenic hiking trails, and serene lakes, making it a popular destination for nature enthusiasts and outdoor activities. Visitors can enjoy camping, fishing, and exploring the park’s rich flora and fauna, providing a tranquil escape from urban life.
Naples Botanical Gardens
Paradise blooms at this tropical flora wonderland. Let the colors from hints of pink to full-on fuchsia dazzle and the tropical fruits tempt all of your senses. Go to extremes with aquatic plants to cacti and succulents and check out the rotating exhibitions and events that entertain and educate.
Sugden Community Theater
Sugden Community Theater in Naples is a vibrant cultural hub renowned for its high-quality theatrical productions and community events. With its state-of-the-art facilities, the theater offers a diverse range of performances, from classic plays to contemporary shows, enriching the local arts scene.
Artis-Naples
Artis-Naples in Naples, Florida, is a premier cultural institution offering a wide array of artistic performances, including music, theater, and visual arts. Home to the Naples Philharmonic and The Baker Museum, it serves as a vibrant center for creative expression and cultural enrichment in the community.
Get Outdoors
Birders, grab your binoculars, because Naples is an access point to the Great Florida Birding Trail where you can spy limpkins, warblers, and even big guys like storks. Kayakers, book a guided tour and hit the waters of Rookery Bay where your guide will loop you through mangrove water paths and teach you about the ecosystem. For the more intrepid outdoor enthusiasts, guided swamp walks are a one-of-a-kind way to explore the only subtropical wilderness in the US.
Spas and Wellness
Grab a mat and bliss out with yoga on the beach or elevate your zen with a session of paddleboard yoga. Soothe those sore muscles with a spa treatment at one of Naples’ retreats. Choose from a menu of body work indulgences at one of the larger spas or plan a visit to one of the smaller, local wellness retreats.
Namba
Premium Grill Selections include mouthwatering Prime Rib Eye, Alaskan King Crab and Whole Tiger Prawn. Known for their meticulous balance of flavors, and exquisitely plated dishes, NAMBA continues to showcase Japanese cuisine to Naples, with innovative flair.
Authentic Tacos at Taqueria San Julian 2
A hole in the wall with fantastic Tacos and Margaritas. Definitely off the beaten path. Fresh salsas made in-house and perfect tacos from chicken, pork, and beef but my favorite is the tongue tacos!
Get to Know Pho at Noodle Saigon
Noodle Saigon is a family-owned Vietnamese restaurant serving Vietnamese cuisine with flair in Naples, Florida. For authentic Vietnamese cuisine, visit our Vietnamese restaurant in Naples, Florida.
Table Grilling at Zen Asian BBQ
Zen features creative and fresh sushi, Thai dishes inspired by Thai Street food, authentic Korean dishes, and their famous Ramen. Their Korean BBQ features premium meats, fish, lobster and vegetables to be cooked by the guest tableside and served with housemade sauces and several side dishes.
Get Your Sandwich on at Pastrami Dan’s
No table service. No drive thru. No wine. No tablecloths. No silverware. No hostess. No valet parking. No credit cards. No pretense. And you get pastrami, roast beef (with gravy) or a taco with chips. What they do here is just as simple but delicious and done well. Eat like a true local!
Brooks Gourmet Burgers and Dogs
Since 2010, Brooks gourmet Burgers & Dogs has been committed to serving the perfect burger. Their all-natural, brilliantly cooked , deliciously crafted burgers are nationally recognized and locally famous.
Homemade Ice Cream at Belgian Yummies
Satisfy your hunger for delicately made confections. At Belgian Yummies in Naples, FL, they have an expansive menu of ice creams, cakes, pies, Authentic Belgian waffles, ice cream pops, and ice cream sandwiches dipped in the finest Belgian chocolate.
Riptide Brewery
Sip on meticulously crafted beers that tell the story of Naples’ flavor palette. From hoppy IPAs to smooth stouts, Riptide’s diverse selection caters to every taste bud.
Bone Hook Brewing Company
Step into a world of flavor and camaraderie as you indulge in the artistry of their handcrafted brews.
Ankrolab
Property Damage Waiver
Enjoy peace-of-mind with our incidental damage protection.
SkyRun includes a property damage protection waiver on each reservation. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure. It does not cover damage that is willful, the result of negligence, or damaged caused by the misuse of household items. It also doesn’t cover unreported damage. SkyRun doesn’t charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is non-refundable.
If during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss”, and the property owner’s insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file. Coverage is provided to you and all travelling companions that are staying in the home overnight during your stay.
Coverage is not provided for loss due to:
- Your intentional acts or gross negligence.
- Any damage that occurs if you are in violation of the terms and conditions (including but not limited to having more than maximum occupancy or having a party).
- Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you.
- Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation unless substantiated by a police report.
Your Duties in the Event of Damage. You must:
- Take all reasonable, necessary steps to protect the property and prevent further damage to it.
- Report the loss in writing (email ok) prior to check-out to the SkyRun staff.
- Provide us documentation such as pictures to substantiate the claim.
Travel Insurance
Nationwide® Travel Insurance protects your vacation investment against unforeseen events like a hurricane, sickness, injury, flight cancellation, job loss and much more.
Group coverage protects everyone in your traveling party for one low price.
Check-In Instructions
SkyRun has done an amazing job with my beach condo. They pay attention to every detail and provide incredible service. They are super responsive and go way above and beyond. In just a very short time they have secured a large number of bookings for my unit. Exceptional company to work with and I highly recommend them.
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